Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H24O |
Molecular Weight | 220.3505 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
InChI
InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N
InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
Molecular Formula | C15H24O |
Molecular Weight | 220.3505 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. BHT is a substituted derivative of phenol. BHT helps to prevent the formation of free radicals and oxidation. When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. It may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). BHT was first used as an antioxidant food additive in 1954. BHT does have other commercial uses, as in animal feeds and in the manufacture of synthetic rubber and plastics, where it also acts as an antioxidant. The U.S. Food and Drug Administration has deemed that BHT is safe enough when used in limited concentrations. It currently permits its use in concentrations of about 0.01% to 0.02% in most foods. As an emulsion stabilizer in shortening, it may be used in a somewhat higher concentration, 200 parts per million.
CNS Activity
Sources: http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=1071&AspxAutoDetectCookieSupport=1
Curator's Comment: It may cross the blood brain barrier, causing psychotropic symptoms
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19231207 |
630.0 nM [Ki] | ||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Inactive ingredient | A-TEAM Approved UseUSE HELPS PROTECT AGAINST SUNBURN Launch Date2014 |
PubMed
Title | Date | PubMed |
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Haemorrhages due to defective blood coagulation do not occur in mice and guinea-pigs fed butylated hydroxytoluene, but nephrotoxicity is found in mice. | 1992 Feb |
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Inhibition by butylated hydroxytoluene and its oxidative metabolites of DMBA-induced mammary tumorigenesis and of mammary DMBA-DNA adduct formation in vivo in the female rat. | 1992 Jun |
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Antioxidizing potency of phenol compounds in olive oil mill wastewater. | 2003 Dec 17 |
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Cytotoxicity and apoptosis induction by butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). | 2003 Nov-Dec |
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[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals]. | 2004 Apr |
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Recovery of phenolic antioxidants from wine industry by-products. | 2004 Apr |
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Inhibition of glutathione S-transferase P1-1 in mouse lung epithelial cells by the tumor promoter 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadienone (BHT-quinone methide): protein adducts investigated by electrospray mass spectrometry. | 2004 Dec |
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Relative amounts of antagonistic splicing factors, hnRNP A1 and ASF/SF2, change during neoplastic lung growth: implications for pre-mRNA processing. | 2004 Dec |
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Mitochondrial permeability transition induced by reactive oxygen species is independent of cholesterol-regulated membrane fluidity. | 2004 Feb 27 |
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Analysis of insecticidal Azadirachta indica A. Juss. fractions. | 2004 Jan-Feb |
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Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites. | 2004 Jul |
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Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress. | 2004 Jun |
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Effect of thiabendazole on some rat hepatic xenobiotic metabolising enzymes. | 2004 Jun |
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Inhibitory effects of organic acid salts on growth of Clostridium perfringens from spore inocula during chilling of marinated ground turkey breast. | 2004 Jun 1 |
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Measurement of anti-HIV activity of marketed vaginal products and excipients using a PBMC-based in vitro assay. | 2004 Mar |
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In vitro estrogenicity of resin composites. | 2004 Mar |
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[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004 May |
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Relative antioxidant capacities of propofol and its main metabolites. | 2004 Nov |
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Optimization of a high-performance liquid chromatography system by artificial neural networks for separation and determination of antioxidants. | 2004 Oct |
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Vanadium-catalyzed sulfenylation of indoles and 2-naphthols with thiols under molecular oxygen. | 2004 Oct 29 |
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Mononuclear, five-coordinate lanthanide amido and aryloxide complexes bearing tetradentate (N2O2) Schiff bases. | 2004 Oct 4 |
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Malondialdehyde, a lipoperoxidation-derived aldehyde, can bring about secondary oxidative damage to proteins. | 2004 Sep |
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Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation. | 2004 Sep 22 |
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Anticancer properties of propofol-docosahexaenoate and propofol-eicosapentaenoate on breast cancer cells. | 2005 |
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2,1,3-Benzothiadiazine derivatives: synthesis and screening versus PDE4 enzyme. | 2005 Aug |
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Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats. | 2005 Aug 15 |
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Method development and validation for monitoring in vivo oxidative stress: evaluation of lipid peroxidation and fat-soluble vitamin status by HPLC in rat plasma. | 2005 Aug 5 |
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Synthesis, biological evaluation and molecular modelling studies on benzothiadiazine derivatives as PDE4 selective inhibitors. | 2005 Feb 15 |
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Synthesis and characterization of BHT-derived tert-butyl dendrons. | 2005 Feb 4 |
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TNF alpha potentiates glutamate neurotoxicity by inhibiting glutamate uptake in organotypic brain slice cultures: neuroprotection by NF kappa B inhibition. | 2005 Feb 9 |
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Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia. | 2005 Jan 26 |
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Single-site anionic polymerization. Monomeric ester enolaluminate propagator synthesis, molecular structure, and polymerization mechanism. | 2005 Jan 26 |
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[Activation of deoxyribonucleotide synthesis by radioprotectants and antioxidants as a key stage in formation of body resistance to DNA-damaging factors]. | 2005 Jul-Aug |
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[Determination of quercetin in apples by reversed-phase high performance liquid chromatography]. | 2005 May |
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Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry. | 2005 Oct |
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Iron-ascorbic acid-induced oxidant stress and its quenching by paraoxonase 1 in HDL and the liver: comparison between humans and rats. | 2005 Oct 1 |
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Scavenging of dpph* radicals by vitamin E is accelerated by its partial ionization: the role of sequential proton loss electron transfer. | 2005 Oct 27 |
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New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents. | 2006 Aug 15 |
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Polypyrroles as antioxidants: kinetic studies on reactions of bilirubin and biliverdin dimethyl esters and synthetic model compounds with peroxyl radicals in solution. Chemical calculations on selected typical structures. | 2006 Jan 6 |
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Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species. | 2006 Jul 1 |
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Attenuation of the pulmonary inflammatory response following butylated hydroxytoluene treatment of cytosolic phospholipase A2 null mice. | 2006 Jun |
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Synthesis and antioxidant activity of [60]fullerene-BHT conjugates. | 2006 Jun 2 |
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Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages. | 2006 Jun 26 |
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Beta-catenin in the fibroproliferative response to acute lung injury. | 2006 Mar |
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Cadmium-induced apoptosis in rat kidney epithelial cells involves decrease in nuclear factor-kappa B activity. | 2006 May |
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Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside. | 2006 May 31 |
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Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. | 2006 May 31 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Quantitative analysis of early chemically-induced pulmonary lesions in mice of varying susceptibilities to lung tumorigenesis. | 2006 Sep 28 |
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Does immune stimulation or antioxidant therapy reduce MNU-induced placental damage via activation of Jak-STAT and NFkappaB signaling pathways? | 2007 May-Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2988845
The effect of topical therapy with 15% Butylated hydroxytoluene in mineral oil on the course of recurrent herpes simplex labialis was examined in 30 patients in a double-blind, placebo-controlled pilot study.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1900157
Curator's Comment: The effect of Butylated hydroxytoluene on the oxidation of low density lipoproteins in relation to prostacyclin synthesis was investigated in the prescence of rabbit smooth muscle cells (SMC) and Fe-containing culture medium.
Butylated hydroxytoluene (BHT) inhibited lipoprotein oxidation by IC50 values of 0.8 uM
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:08:02 GMT 2023
by
admin
on
Fri Dec 15 15:08:02 GMT 2023
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Record UNII |
1P9D0Z171K
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
22105
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JECFA EVALUATION |
INS-321
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CODEX ALIMENTARIUS (GSFA) |
INS-321
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NCI_THESAURUS |
C275
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CFR |
21 CFR 172.115
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34247
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m2820
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PRIMARY | Merck Index | ||
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100000076384
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CHEMBL146
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6347
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D002084
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SUB11765MIG
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1082708
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C322
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1P9D0Z171K
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1P9D0Z171K
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128-37-0
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204-881-4
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DTXSID2020216
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BUTYLATED HYDROXYTOLUENE
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1848
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1147
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31404
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BUTYLATED HYDROXYTOLUENE
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PRIMARY | Description: Colourless crystals or a white or almost white, crystalline powder; odour, faint and characteristic. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS, acetone R, ether R, and arachis oil R. Category: Antioxidant. Storage: Butylated hydroxytoluene should be kept in a well-closed container, protected from light. |
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.65.pdf
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